The All New Ashton Kutcher Story!

It is a plain, sunny morning in Burbank, California, and Ashton Kutcher, ever in a cardigan, wearing one of those winter hats that sit on his head like a potato sack pulled back to the neck, is singing "I'm a douche!" He's dancing to it, even. Sort of. Flouncing, more like. One-two-three-four. Four steps up, lock arms with a homeless person on the street set, do-si-do with the woman pushing a grocery cart, keep going. "I'm a douche!" He's lip-synching, actually.

He's not, of course. A douche. It's a line asserted in character, his character, at the front of the chorus, a full-out song-and-dance routine for Two and a Half Men, the marathon megahit that he famously became one of the men on a year and a half ago. Everyone in the street — policeman, pedestrian, passerby — is a part of the number, getting caught up in Kutcher's character's revelation. Each of them telling him the same thing: "You're a douche!" They keep saying it, that word, repeated over and over again until it is meaningless. Its utterance probably still qualifies as a middling network-television surprise, but in this case it's a trigger for this flash-mob dance number, to be shot for real a few days hence and broadcast on CBS in three weeks.

Ashton Kutcher is playing the butt of the joke, and he's cool with that. Loose-limbed, without much rhythm, taking steps that are too big or too small, depending on what the choreographer shouts at any given moment, he works through it blithely, willingly, swiftly, always hinting at a smile. People love it when he smiles. The members of the chorus line wait for it. Everything he says gets repeated from front to back. He radiates modesty. They are giddy. Kutcher is happy, occupied by the work of things, doing his best to learn the routine just well enough that he can use it for laughs. Right now, he's amusing mostly himself, since he'll be the first to tell you: He is no song-and-dance man. That's fine; he likes laughing and making people laugh. That's one of his jobs. It is and will always be his first job.

The outline of his cell phone is visible in the right front pocket of his pants. He checks it five times in the next three hours: just before a read-through, from the corner of the show's main living-room set, from the half shell of an unlit airplane set, twice more during quick breaks in which furniture is rolled on or off. He checks his phone in retreat, without interrupting the various confluences of the rehearsal. He is discreet. Always. That phone is the ever-present physical representation of his second job: Ashton Kutcher, venture capitalist. The job in which he concentrates on changing the world, one Internet start-up at a time. He takes that job just as seriously as his first one. More, maybe.

Today, on job one, he's playing straight man to the theatrically hungry Jon Cryer, who for almost eight years worked opposite Charlie Sheen, the one-and-no-half man who finally ping-ponged his nutty ass off the set of one of the longest-running shows in recent CBS history — ten years now — opening up room for the douche ex machina arrival of Kutcher's character, a fictional billionaire who is sometimes frustrated by the way gosh-darned money changes people's perception of him. When Sheen's character miraculously died, Kutcher's popped up to recomplete the titular mathematics of the show.

But let's be clear: Kutcher's character, the billionaire Walden something, has a private jet at his beck and call. A rehearsal for a scene in this very episode, the one with the song-and-dance bit, takes place on that jet, with a giant buffet of shrimp that the two men (Kutcher and Cryer) share while flying to see a girl Walden may love, to whom he lied about the nature of his work, having claimed to be a Christmas-tree salesman. Liar. And a jet? A giant buffet of giant shrimp or two? We all know what that makes him.

Hence the song.

But again: That ain't Ashton Kutcher. No douche he. He is something else entirely. A circuit of things really. Shambling, loose-shouldered frumpster. A television star who succeeded first by playing an undeniably likable, weirdly unaccountable doper on That '70s Show, and who now plays an undeniably likable, vaguely unaccountable billionaire on his current show. The soon-to-be-official former husband of Demi Moore, current boyfriend of Mila Kunis, the guy who gets women, great ones. A well-known tech enthusiast, he drove Twitter almost from the get-go, creating a public version of himself that had to do only with his private life, making him among the first to tell anyone who would tune in what band he was listening to on Spotify, that he had just run out of gas, and that his wife was pressing his suit while wearing a bikini. He helped make Twitter a thing. Now everyone tweets. Kutcher, not so much anymore. His life with Moore is over, and he's content not to speak about his relationship with Kunis. Tweeting doesn't serve anymore. Perhaps more than anything, he's a guy looking for the next thing, searching for a way to think about human need in the near future, an active investor in venture-capital schemes. He's more investor than actor now, probably. Futurist. Bears fan. Dog owner.

And he's a movie star who has yet to make a movie worth remembering. That may change with the release next month of Jobs, the Steve Jobs biopic in which Kutcher stars. It is a movie both culturally called for and up his alley, subjectwise. He is confident about it, not anxious, eager for its release. It's just more work. And no matter what you think of Ashton Kutcher, know this much: He loves work. Loves it like an immigrant, loves it like a rich man, loves it like everybody in between.

Continues on -->...

Nigel Parry

Nigel Parry

Jacket and shirt by Giorgio Armani; trousers by Armani Exchange; tie by Bespoken.

Nigel Parry

Kutcher doesn't have much time. Not today. Not any day, really. He moves from dance rehearsal to read-through to walk-through rehearsal and blocking, skips lunch, and presses on with rewrites through the afternoon. He is free at 4:30 P.M. for a meeting at his house. But he has dinner at 6:00 with a venture-capital client. It doesn't faze him, this schedule, and he doesn't expect that it should faze anyone else. He works, like anyone else.

"This is not new. I've always been busy like this," he says. "When I was on the '70s show, I had that and I had Punk'd and I had my own production company. That pretty much sealed up all my time." When Kutcher looks at you, there is always an undercurrent of amazement in his gaze. It isn't modesty, though he is plenty modest. And the blankness he sometimes lends his characters, which makes them feel a little dopey or naive? Call it productive understatement. When asked, Why venture capital? Why not poker? Or sports betting? Kutcher pauses, goes flat, and states the existence of an unknown chapter in his life of work as if he were declaring a record of his immunizations.

"I actually used to be a front for the largest national sports-betting syndicate in America."

Eh? Kutcher is prone to repeat things when he likes the construction of an answer. It gives him time to figure out how much he wants to explain. So he says it again, pretty much the same words, more quickly this time and a little softer.

"I was a front for the largest sports-betting syndicate in America."

He deadpans it, as if it were a minor role in a forgotten movie, so one is tempted not to take it seriously. When asked to elaborate, when pushed, Kutcher cracks the story right open around an explanation of the forces at work: "In football, you're basically looking for numerical anomalies. Handicappers have to handicap X number of games every week, which is why the sport — college football in particular — is really good for this, because there's such a broad array of games happening at one time. The handicappers can only handicap so many games really well. And all they're really trying to do, as the house is, is to keep an even number of people on either side of the bet, so they get the juice, right?"

Now he's elbows on knees, leaning forward into the story he's telling. "So if you can find the anomaly where the assumption is they're going to get heavy on one side, when the line moves it can actually move favorably as it pertains to the potential outcome of the game. So you set a margin of error against the line. If they've set it inaccurately, too hard to one side, you gauge that and play the other side of the line. You can gain probably a 40 percent statistical advantage on them. It's really complicated. You gotta know a lot of data points — how this team played on various surfaces, in different weather — a lot. But these guys could do it."

He sits back.

"So, generally these types of individuals aren't allowed to gamble, but they know how to handicap the house. So they sent me in. I basically just placed the bet."

How long did that go on?

"One season," he says. "Well, half a season."

They got on to you that fast?

"We were clearing, like, $750,000 in four weeks of college football. It was pretty fun. Then they caught on. The hypothesis had been that the house would just assume that I was a dumb actor with a lot of money who liked football."

So, dumb actor playing dumb actor? Kutcher was born a dumb-actor savant: the good looks purposefully blanketed by obtuseness, the wincing stare from under the bill of a ball cap, the glassy-eyed amazement, the vague mouth breathing. He demands that you not take him seriously, which is, of course, exactly what he needs from the world, because it allows him to take the world and its machinations very seriously.

Nigel Parry

Nigel Parry

Jacket and Shirt by Giorgio Armani; Trousers by Armani Exchange; Tie by Bespoken; Monk-Straps by Bally.

On the set, in between scene work, line readings, and blocking suggestions, Kutcher stares into his phone, texts unknown parties, scans the news, browses market reports. He is not rude about it; the people around him seem to expect no less. He sits at some distance from the other cast members when he is not involved in a scene, and works his second job right in the middle of the first. And while it may not sound like it, the effect is less isolated than it is engaged. No one seems to begrudge him his energy. But he doesn't hold the phone down low or glance at it sideways as if it were some undeniable surprise. Everyone knows. He has another life on the other end of that phone.

At one point, the director stands close to him and asks a question about a small company Kutcher invested in. There are murmurs, then some laughter. The director throws his hands in the air, and Kutcher gives him the dumb-actor head tilt, then the dumb-actor smile, which seems to crack from beneath a previous dumb-actor smile. Later he explains: "His wife had been asking him about Uber, which is this great company that makes anyone with a car into an agent, and you don't have to have a limousine service. You just use your phone. She has a broken arm now, and she just Ubers around L.A. She likes it. So she was wondering if she could get in on the investment. But I had to say, 'That boat's kinda sailed.'" Dumb-actor exhale here, dumb-actor puzzled laugh, then a serious declaration: "For a while now."

Later, while rehearsing the scene on the jet-plane set, Kutcher looks up from his phone and says, "The pope opened a Twitter account today." The massive triviality of this news, coming from the mouth of Mr. Twitter himself, sets off a hail of one-liners from Cryer and the set crew. Kutcher laughs, but keeps thumbing down the screen of his phone. When asked later if he — as the onetime pope of Twitter — got the news that the Holy Father has joined Twitter from a Twitter feed, he shakes his head.

"I actually wasn't on Twitter," he said. "I have this kid who collects information from the Internet for me. That's where I saw the pope thing. Just a daily headline roundup: what's happening on the Web, what companies are buying and selling, what the big companies are doing. Generally it's redundant — I get it in the morning news. But every once in a while, something happens that I didn't catch up to: Big segment shifts that are happening like, you know, when Apple went vertical with maps, then Amazon acquires a maps company, and then Google has their maps company up and you start to see all of these companies that have hardware verticals and software verticals developing out their own maps. That might mean an open market segment for map APIs that can go cross-platform, and when you see something like that, when we meet with companies that are pitching my fund — or whatever it might be — that information can be really, really valuable to have. So I was reading just a daily roundup of headlines, an information-building system for me."

Or, as a dumb actor might have said, "The pope opened a Twitter account today," and left it at that.

Nigel Parry

What's fun about Ashton Kutcher? It's a relevant question because it's one of the few things he will make an argument for: that he is fun. "I have fun. I like to snowboard, I love hiking, I like the beach, I'm a good vacationer. I'll watch football with my friends; we'll tear things up." Okay, fun.

He likes his evenings. "For me, the most entertaining evening would be to go sit with entrepreneurs and talk with them about how they're building their companies and how we can help to make them better. That's the one thing in the world — well, I love doing that. And my second idea of a fun evening would be to go to Two and a Half Men and shoot a show in front of a live audience. That sounds like a good time to me. So. I don't go out much. I don't." So he likes his evenings because he can work. Not really fun at all.

He drinks Mexican beer. Marginally fun.

He has a signed Matt Forte helmet on his kitchen counter. There are more helmets downstairs. Vaguely fun.

He loves pro football, grew up in Iowa, in a house divided among NFC North loyalties. "My mom's whole side of the family, they're all Packers fans. My mom's a Bears fan. My stepdad is a Vikings guy. So that gets ugly. My mom sits upstairs watching the Bears game; he sits in the basement. They can't watch it together. Football's a violent anger in our family dynamic." He smiles when he says it. It's a broad Cheshire grin, spread slowly, conspiratorially. He wants you in on it. Kind of fun.

He refers to the Bears in the first-person plural, as in, "Our defense is playing like a stud. We have to get more expansive in our passing." He laments the Bears' quarterback situation, even offers that he'd like to get a chance to work with Jay Cutler, the taciturn and erratic QB. Like any good fan, he believes he himself might have a role to serve. "I'd love to meet him, talk to him. Because I think he doesn't do himself any service with his attitude. I don't think it's a bad attitude. I just think it's the way he projects what he's feeling. I don't think it's a matter of him thinking the wrong thing in the absence of the right thing. And I think there's a way to project it, a certain way, and, you know, I would just like to get with him and work. He's really fucking hard on himself. And I think I get that. That's an aspect of me. I mean, writers on the show are always changing a line or something. And they're looking at me, because I really grind the changes immediately. They'll ask, 'Hey, what's the matter? You all right?' And I'll snap at them: 'I think I can do it better. I can do that better — fuck, man, I gotta do that right.' They say it was fine. I say fuck no. I can't be fun to be around. I apologize. But it's unpleasant. I have to work against that demanding part of me." So, not fun.

Much of the furniture in his house is set low to the ground, like those lounge couches in dance clubs. But you never know if you should lean back, sit forward, or lie down. For his part, Kutcher sits forward, knees bent, back straight. It's easy for him, he's thirty-five, but he seems demonstrably younger. Any position whatsoever.

The oversized windows allow a view of Lake Hollywood. This inspires his declared aspirations. "I want to become a park ranger," Kutcher says, smirking. "That's the only way I can use the lake. It's a rule." This earns him a blank look. "That way I can fish," he says. He's laughing now but pretending that he's trying not to. No one can fish in the lake. Not even the rangers. He seems to know this. He is playing both serious and naive. Seriously naive. That's his bit, because in truth he is neither in any great measure. He might actually do it. Ashton Kutcher is to be believed. Fun to consider.

He has a dog, a graying mutt named Willy Wonka that he calls by both names every time he speaks to him. As in: "Let's go, Willy Wonka" or "Come inside, Willy Wonka." He speaks the dog's name with zero calculation, without affect or preciousness. At one point, he holds the dog gently by the scruff and says, "You gotta have a dog, you know?" Not particularly fun, but correct.

Kutcher truly embodies Steve Jobs in Jobs.

Then there is the record of his work. The only good movie he's ever starred in is Dude, Where's My Car? the picaresque stoner precursor to a dozen Harold & Kumar 420 buddy flicks. Then there's some dreck: What Happens in Vegas, Valentine's Day, New Year's Eve. They made money and not much else.

"I know exactly what films I've done that fucking suck donkey," Kutcher says. "And I know the ones that are good, that people like. And I know it not because of the box office, because the box office is not going to tell you the truth. I know it because I have friends that don't hold back. They don't depend on me for money or employment. They're just friends. Friends tell the truth."

He continues, sitting forward on the low couch: "My big thing is, Fail fast. If you're going to fuck up, get it over with. That's one of the things I talk to the companies about, the ones we work with. I'm like, Look, it didn't work. Fine. Move on. It's a tricky thing to figure out, which is when you ask yourself, Am I at the precipice of success or walking down the wrong road? Because the greatest obstacle always comes right before the breakthrough. And you're always trying to determine which is which. Is this the greatest obstacle? Is it the breakthrough itself? Or is it time to go the other way? That's when you have to surround yourself with brutally honest people who will be like, 'Dude, you suck at this. Stop.' I have, like, two or three really strong data nodes that I know will tell me: 'I don't get it.'"

Yes, he just called his friends "data nodes."

"It's input. They're people. People. People that are giving you information you can trust as accurate, generous, careful. They're not just going to flippantly tell you, 'Eh, that doesn't work,' or they're not just going to tell you 'Yes!' just because that's what you want to hear. To me, that's a valuable piece of data. That's a valuable data chip."

Now he has called advice from his friends "data chips."

"I know who these people are in my life. Partners, friends, coworkers. You have a movie and you show it to them, and if it sucks you want them to be like, 'Dude, that kind of blows.'"

Nigel Parry

When Kutcher lights up a Marlboro. He stands and walks to the corner of his living room and slides the deck doors open for a breeze. He's wearing new clothes — the cardigan, the checked shirt beneath it — that look like old clothes. Or maybe they're just well-tended old clothes. He's heading to a dinner meeting later. It seems unlikely he will change for that. He acted in them this morning, he hosted a visitor wearing them, he'll work in them tonight. He looks like every character he's ever played, which means he's either all actor or no actor at all.

He's willing to admit that he himself has faith in his new movie,the Jobs biopic, which premiered at the Sundance Film Festival in January. Kutcher plays the man himself, and he absolutely inhabits the role. Yeah, he looks like him. Purses his lips like him. Walks with Jobs's unusual gait, a kind of limp. The film itself relies heavily on the use of montage to zip through Jobs's remarkable life, but Kutcher, who is in every frame, anchors it, slows it down — his facial twitches and sidelong glances become significant points of action. "Jobs was an extraordinary guy, but a very ordinary guy in many ways," he says. "There was this one speech that I found where he said, 'So when you grow up, if you spend your life trying not to bounce into walls, just inheriting what you get, you gotta know your life can be a lot broader than that. Once you realize one simple thing: Everything around you that you call life was made by people who are no smarter than you. And you can change it. You can influence it. You can build your own things that other people can use.' And I heard that and I knew exactly what the niche for making the movie was, what the social need for making the movie was. For people seeking purpose. I remember growing up and looking at the world and going, Okay, how do I live in this? instead of How do I create it? How do I build it? How do I make something? And the empowerment of these ideas, I think they make an important story."

He screened the final cut of the movie two weeks ago. "I think it turned out really well," he says. That's all he'll offer. He is acting as a data chip now. Offering input. Very little. He is playing the data chip and trusting that will be enough.

Time grows short. His dinner meeting approaches. More work. Kutcher ignores the clock, though, allowing the conversation to drift. This is work too, after all. Eventually, however, he will be late. He tips back his Mexican beer.

"Whenever we get anxious, it's related to time," he says. "'We're running out of time!' It's the oldest trick in movies — 'Look at the ticking clock! It's a countdown!'" Anxiety, stress, in orbit around time. But Kutcher is inured to time, unpanicked by the moment. "True luxury is being able to own your time — to be able to take a walk, sit on your porch, read the paper, not take the call, not be compelled by obligation."

His axioms of time drive his investment strategy. "I see three categories. I look for companies that create efficiencies of time — service companies that make things quicker, that compress time. Then entertainment, games, movies that make time more intense, more intensely enjoyed. And finally, I look for companies that actually work to create more time for people, through medicine, extending longevity. Health care. I think really successful businesses fall into these three categories. Time is the one thing we only have so much of, and we don't really know how much we have, actually. So assigning value to time is very reasonable and almost easy to do. I invest in that value."

Willy Wonka enters the room. Kutcher greets the dog with an ear rub. "I think you can look at money as a compound manifestation of some piece of time. That value changes when you produce intensely wonderful experiences out of time, provide extremely efficient service, or extend the longevity of someone's time. That affects value. And the higher you get on the value chain of one of those three ideas, the more you are affecting time. The thing I really want to get into is health and wellness, actually creating some level of longevity, finding new time for people. Maybe we'll be lucky enough to be the generation that lives infinitely because we'll have bodies tended by nanobots and gene therapy, eliminating free radicals, helping our DNA."

Question stands: Does Kutcher really want to be what he appears to be: forever young? He twists this one awhile. Nah. "I certainly don't think I'm deserving of taking up space forever as a human. There's a whole generation of people yet to be born that are going to be so much more evolved than I am. I don't want to take up space. They're going to be better equipped to make the world a better place than I am."

So he's off now, to dinner and a conversation with a potential investment client. The aforementioned most entertaining evening ever. Out to the street with Willy Wonka, he says goodbye. He doesn't look even slightly tired, though it has to be exhausting: two full-time jobs, working dinners, dinners with strangers set at the end of long days of work. It has to be asked: Do you really like this stuff? Do you love it?

Kutcher is silent. He tilts his head, gives things a squint. It looks a little like it stings. Lousy question? Question he was worried about?

"Well," he says, "it's a weird question to ask. Do I like what I'm doing?"

Come on. People ask that all the time. Do you like your job? Are you happy with what you are doing? It's a thing in life.

He sees the point. "Okay," he says. "It's a weird question to ask me, 'cause I kinda only do what I like to do."

He declares this truth with his hands in his pants pockets. The world seems completely obvious then. The sun falls behind his house. Kutcher is late to dinner, but he doesn't worry that. He knows what he is. He'll tell. In that way, he is just his own data node, feeding himself the truth.

Nigel Parry

Nigel Parry

Suit by Giorgio Armani; Shirt by Emporio Armani; Tie by Gant.

THINGS YOU PERHAPS DON'T KNOW ABOUT ASHTON K.

He was born in Cedar Rapids, Iowa, on February 7, 1978.

He has a fraternal twin, Michael.

Kutcher has two webbed toes.

He majored in biochemical engineering at the University of Iowa before dropping out to become a model. He has said he wanted to research cardiomyopathy to try to cure his brother's heart condition.

To make money during college, he worked at General Mills, sweeping floors.

He was a member of the Delta Chi fraternity. Same as Kevin Costner, incidentally.

Kutcher is the highest-paid actor on television. He is estimated to have made $24 million between May 2011 and May 2012.

His character on the show, a tech investor, has plugged some of the companies that Kutcher has invested in in real life, including Foursquare, Hipmunk, and Flipboard.

Kutcher is reported to have made investments in at least twenty-seven technology companies. His more notable ventures include Skype, Spotify, and Airbnb.

He approaches potential investments the way he approaches reading a script, breaking down the company's objectives the same way he would analyze a character's motivations.

At seventeen, he bet a friend $1,000 that someday he would go on a date with Jennifer Aniston. When he asked her five years later, she declined.

Kutcher is set to ride the Virgin Galactic, the world's first commercial space line, when it launches in December.

His real first name is Christopher.

This content is created and maintained by a third party, and imported onto this page to help users provide their email addresses. You may be able to find more information about this and similar content at piano.io

This commenting section is created and maintained by a third party, and imported onto this page. You may be able to find more information on their web site.

A Part of Hearst Digital Media
Esquire participates in various affiliate marketing programs, which means we may get paid commissions on editorially chosen products purchased through our links to retailer sites.